DE2022503B2 - Benzodiazepine und Verfahren zu ihrer Herste,Jung - Google Patents
Benzodiazepine und Verfahren zu ihrer Herste,JungInfo
- Publication number
- DE2022503B2 DE2022503B2 DE2022503A DE2022503A DE2022503B2 DE 2022503 B2 DE2022503 B2 DE 2022503B2 DE 2022503 A DE2022503 A DE 2022503A DE 2022503 A DE2022503 A DE 2022503A DE 2022503 B2 DE2022503 B2 DE 2022503B2
- Authority
- DE
- Germany
- Prior art keywords
- dihydro
- benzodiazepin
- mol
- phenyl
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001557 benzodiazepines Chemical class 0.000 title claims description 9
- 229940049706 benzodiazepine Drugs 0.000 title claims description 8
- 238000000034 method Methods 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000008096 xylene Substances 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000005662 Paraffin oil Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- -1 alkyl radical Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- AKPLHCDWDRPJGD-UHFFFAOYSA-N nordazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 AKPLHCDWDRPJGD-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VACOMSNNWGXHSF-UHFFFAOYSA-N chloro(dimethylphosphoryl)methane Chemical compound CP(C)(=O)CCl VACOMSNNWGXHSF-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 description 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical class NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- LRKANDQWBAVWMW-UHFFFAOYSA-N bromo(dimethylphosphoryl)methane Chemical compound CP(C)(=O)CBr LRKANDQWBAVWMW-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 2
- 229960003529 diazepam Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VPMXFLSYFJVOGW-UHFFFAOYSA-N 1-chloro-2-dimethylphosphorylethane Chemical compound CP(C)(=O)CCCl VPMXFLSYFJVOGW-UHFFFAOYSA-N 0.000 description 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
- AHSJZIFUGYWAJM-UHFFFAOYSA-N 2-methylsulfonyloxypropan-2-yl-oxido-oxophosphanium Chemical compound CC(P(=O)=O)(C)OS(=O)(=O)C AHSJZIFUGYWAJM-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- BUCORZSTKDOEKQ-UHFFFAOYSA-N 7-chloro-4-hydroxy-N-methyl-5-phenyl-3H-1,4-benzodiazepin-2-imine Chemical group C=12C=C(Cl)C=CC2=NC(=NC)CN(O)C=1C1=CC=CC=C1 BUCORZSTKDOEKQ-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- 229960004782 chlordiazepoxide Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000002566 clonic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- HGDIHUZVQPKSMO-UHFFFAOYSA-N methylphosphonoylmethane Chemical group CP(C)=O HGDIHUZVQPKSMO-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- UUBMOUNXQFMBQF-UHFFFAOYSA-N ro5-2904 Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 UUBMOUNXQFMBQF-UHFFFAOYSA-N 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical compound [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5304—Acyclic saturated phosphine oxides or thioxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (34)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2022503A DE2022503B2 (de) | 1970-05-08 | 1970-05-08 | Benzodiazepine und Verfahren zu ihrer Herste,Jung |
| BE765790A BE765790A (fr) | 1970-05-08 | 1971-04-15 | Benzodiazepines et leur preparation |
| HUHO1374A HU162803B (ref) | 1970-05-08 | 1971-04-29 | |
| BG021646A BG20801A3 (bg) | 1970-05-08 | 1971-05-04 | Метод за получаване на бензодиазепини |
| BG017459A BG19171A3 (bg) | 1970-05-08 | 1971-05-04 | Метод за получаване на бензодиазепин |
| CH630974A CH552019A (de) | 1970-05-08 | 1971-05-05 | Verfahren zur herstellung von benzodiazepinen. |
| CS7600001395A CS183648B2 (en) | 1970-05-08 | 1971-05-05 | Method of producing derivatives of benzodiazepine |
| CH631074A CH552020A (de) | 1970-05-08 | 1971-05-05 | Verfahren zur herstellung von benzodiazepinen. |
| ES390892A ES390892A1 (es) | 1970-05-08 | 1971-05-05 | Procedimiento para la preparacion de benzodiazepinas. |
| GB1320771*[A GB1345443A (en) | 1970-05-08 | 1971-05-05 | 1-dialkylphosphinylalkyl-2-oxo-5-alkylphenyl-1,2-dihydro-3h- benzo-1,4-diazepines |
| CS7100003260A CS183621B2 (en) | 1970-05-08 | 1971-05-05 | Method for producing benzodiazepine derivatives |
| CS7500004194A CS183635B2 (en) | 1970-05-08 | 1971-05-05 | Production method of benzodiazepine derivatives |
| CH664171A CH552632A (de) | 1970-05-08 | 1971-05-05 | Verfahren zur herstellung von benzodiazepinen. |
| RO7100066817A RO61737A (fr) | 1970-05-08 | 1971-05-06 | Procede pour la preparation des derives du benzodiazepine |
| US00140977A US3738982A (en) | 1970-05-08 | 1971-05-06 | 1,3-dihydro-1 oxophosphinylalkyl-2h-1,4-benzodiazepine-2-ones |
| FI711266A FI51696C (fi) | 1970-05-08 | 1971-05-06 | Menetelmä 1-dialkyylifosfinyylialkyyli-5-fenyyli-1,3-dihydro-2H-1,4-be ntsodiatsepin-2-onien valmistamiseksi, joilla on rauhoittava vaikutus. |
| SE7105874A SE374115B (ref) | 1970-05-08 | 1971-05-06 | |
| NL7106239A NL7106239A (ref) | 1970-05-08 | 1971-05-06 | |
| IT24198/71A IT1037030B (it) | 1970-05-08 | 1971-05-06 | Benzodiazepine e processo per la loro preparazione |
| DK220771A DK137861C (da) | 1970-05-08 | 1971-05-06 | Fremgangsmaade til fremstilling af 1,4-benzodiazepinderivater |
| IL36789A IL36789A (en) | 1970-05-08 | 1971-05-06 | 1-oxophosphinylalkyl-benzodiazepines and process for preparing them |
| SU1746380A SU425398A3 (ru) | 1970-05-08 | 1971-05-07 | СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ БЕНЗОДИАЗЕПИНА1Предлагаетс способ получени новых фос- форилированных производных .бензодиазепи- на, обладающих ценными фармакологическими свойствами.Основанный на известной в химии бензо- 5 диазепинов реакции способ позвол ет получить новые соединени , обладающие лучшими свойствами, чем известные соединени подобного действи .Предлагаемый способ получени производ- 10 ных бензодиазепина общей формулыКз обозначает линейный или разветвленный алкильный радикал, содержащий 1—3 атома углерода;п — целое число 1—б, заключаетс в том, что о-аминобензофенон общей формулы15(Oi^kPlRslr 'NH О О•Rгде RI и R2 представл ют собой одинаковые или различные заместители и обозначают атом водорода, галоид, нитрогруппу или три- фторметильный радикал, кроме того, Rz может быть также линейным или разветвленным алкильным радикалом, содержащим 1—6 атомов углерода;где RI, RZ, Rs и п имеют приведенные значени ,20 подвергают взаимодействию с производным аминоуксусной кислоты, преимущественно с эфиром, или последовательно .подвергают взаимодействию с галоидангидридом галоидук- сусной кислоты, затем с аммиаком и циклизу-25 ют. Целевой продукт выдел ют в свободном состо нии или в виде соли известными приемами. Циклизацию осуществл ют, например, с помощью пиридина. Пример. 6,4 г 5-хлор-2-(Ы-диметилоксо-30 фосфинилметил)-аминобензофенона (т. пл. |
| AT604972A AT308128B (de) | 1970-05-08 | 1971-05-07 | Verfahren zur Herstellung neuen Benzodiazepinen |
| PL1971148004A PL81616B1 (ref) | 1970-05-08 | 1971-05-07 | |
| ZA712965A ZA712965B (en) | 1970-05-08 | 1971-05-07 | Benzodiazepines and process for preparing them |
| IE575/71A IE35197B1 (en) | 1970-05-08 | 1971-05-07 | 1-dialkylphosphinylalkyl-2-oxo-5-alkylphenyl-1,2-dihydro-3h-benzo-(1,4)-diazepines |
| DD164731A DD97348A5 (ref) | 1970-05-08 | 1971-05-07 | |
| FR7116571A FR2100639B1 (ref) | 1970-05-08 | 1971-05-07 | |
| SU1666803A SU366615A1 (ru) | 1971-05-07 | СССРПриоритет 08.V.1970, № р 2022503.0, ФРГ 23.IX.1970, № Р 2046848.8, ФРГОпубликовано 16.1.1973. Бюллетень № 7 Дата опубликовани описани 11.VI.1973М. Кл. С 07f 9/50 С 07d 53/06УДК 547.341.07(088.8) | |
| PL1971175328A PL86507B1 (ref) | 1970-05-08 | 1971-05-07 | |
| NO01727/71A NO130399B (ref) | 1970-05-08 | 1971-05-07 | |
| AT398871A AT308121B (de) | 1970-05-08 | 1971-05-07 | Verfahren zur Herstellung von neuen Benzodiazepinen |
| US00340209A US3849559A (en) | 1970-05-08 | 1973-03-12 | Tranquilizer composition and method of treatment |
| DK442473A DK138543C (da) | 1970-05-08 | 1973-08-10 | Analogifremgangsmaade til fremstilling af 1,4-benzodiazepinderivater |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2022503A DE2022503B2 (de) | 1970-05-08 | 1970-05-08 | Benzodiazepine und Verfahren zu ihrer Herste,Jung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2022503A1 DE2022503A1 (de) | 1971-11-25 |
| DE2022503B2 true DE2022503B2 (de) | 1974-03-28 |
| DE2022503C3 DE2022503C3 (ref) | 1974-11-28 |
Family
ID=5770570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2022503A Granted DE2022503B2 (de) | 1970-05-08 | 1970-05-08 | Benzodiazepine und Verfahren zu ihrer Herste,Jung |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2022503B2 (ref) |
| ZA (1) | ZA712965B (ref) |
-
1970
- 1970-05-08 DE DE2022503A patent/DE2022503B2/de active Granted
-
1971
- 1971-05-07 ZA ZA712965A patent/ZA712965B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA712965B (en) | 1972-01-26 |
| DE2022503C3 (ref) | 1974-11-28 |
| DE2022503A1 (de) | 1971-11-25 |
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| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |